Wired 25: The 25 Best Hip-Hop Moments From Chappelle’s Show [VIDEOS]
Written by
Kazeem Famuyide
Published on
January 22, 2013
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Get ready to feel extremely old. On January 22nd 2003, Chappelle’s Showmade its debut on Comedy Central.
Today marks the ten year anniversary of the debut of Dave Chappelle’s wildly popular sketch comedy show. The controversial show starring the stand-up comedian is still one of the funniest television shows ever to air.
The show pushed the boundaries of what was allowed and not allowed on cable television as Chappelle shined a humorous light on race relations, pop culture, politics and everything in between.
What we’ll never forget about Chappelle is the stage that he always gave Hip-Hop. It was one thing to include Hip-Hop artists as performers on the show, but it was the comedian’s use of the artists in the sketches that made for some truly unforgettable. Dave’s ability to equally satirize some of the most iconic artists in Hip-Hop also added to what made Chappelle’s Show the benchmark in sketch comedy television.
In no particular order, take a look at some of the most hilarious Hip-Hop moments in the history of Chappelle’s Show. We miss ya, Dave!
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Photo: Tumblr
“The Racial Draft”
With guest stars Mos Def, Angie Martinez and the Wu-Tang Clan; Chappelle’s Show decided once and for all who can claim what nationality in the “Racial Draft.”
“Lil Jon In Love”
Dave Chappelle as Lil Jon took a dramatic turn in this love story with Susan Sarandon.
“C’mon T***y!”
On the debut episode of the show, Chappelle satirized a popular Mitsubishi commercial with how he would have made the commercial.
Nat King Cole Christmas
Nat King Cole gets a little bit disrespectful to the females for his upcoming Christmas album, while sipping on the finest Dom P.
“Reparations 2003”
Black people got reparations and everyone lost their minds.
“Roc-a-Pads”
Dame Dash and a young Rashida Jones star in this informercial for “Roc-A-Pads.”
“Redman’s Potty Fresh”
Redman shoots a commercial for toilet cleaner that is made of “enzymes and s**t.”
“The Dave Chappelle Story”
Dave Chappelle pulls an Antoine Fisher and directs, writes and stars in his own autobiographical movie.
“The Mad Real World”
What happens when things get “mad real?”
“Wu-Tang Financial”
RZA and GZA implore you to diversify your bonds, ni**a.
“R. Kelly – Piss On You”
You don’t really want to know what happens at an R. Kelly party. Drip, drip, drip.
“Turn My Headphones Up!”
Funkmaster Flex co-signs the latest rapper to get shot and live to tell about it. Just make sure to turn his headphones up.
“White People Can Dance”
John Mayer and Questlove join Dave Chappelle’s quest to find music that white people can dance to.
Charlie Murphy’s True Hollywood Stories – Prince
Prince’s basketball exploits were immortalized in this classic sketch.
Charlie Murphy’s True Hollywood Stories – Rick James
You’ve seen this.
“A Moment In The Life Of Lil’ Jon”
Lil’ Jon meets “Lil Jon.”
“Making The Band”
Da Band, Wyclef Jean, “Diddy” and “Fonzworth Bentley” star in this spoof of the popular MTV show.
“Celebrity Trial Jury”
Dave Chappelle comes to the defense of Michael Jackson and R.Kelly in this hilarious sketch.
“The Playa Haters Ball”
Ice T is the host of the annual Playa Haters Ball.
“Method Man Torture”
Chappelle acts out the memorable sketch before the Method Man’s breakout single.
“MTV Cribs”
Chappelle shows off his new baller life after signing his record contract with Comedy Central.
“Tupac Lives”
We kind of get the idea that Tupac isn’t dead.
Big Boi Performs “The Rooster”
Big Boi performs this cut off of the classic album, SpeakerBoxxx/The Love Below.
DMX Doesn’t Stop Performing
DMX literally will not stop performing.
Mos Def Rides Shotgun
The first musical performance from the classic show took place in Dave’s car.
Bonus: Kanye West, Mos Def and Freeway Perform “Two Words”
